Conjugate addition to unsaturated nitriles are notoriously difficult, preventing conjugate addition-alkylation-annulation strategies. This presentation describes an intermolecular conjugate addition to cyclic unsaturated nitriles in aqueous media. The radicaloid conditions allow functionalized nucleophile bearing a pendant electrophile for subsequent intramolecular alkylation which provides a fundamentally new annulation strategy with cyclic alkene nitriles through sequential conjugate addition-cuprate cyclization.
New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster